AM-411

AM-411
Identifiers
	IUPAC name (6aR,10aR)-3-(1-Adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	212835-02-4 ;
PubChem CID	9799945;
ChemSpider	7975710 ;
ChEMBL	ChEMBL434351 ;
Chemical and physical data
Formula	C26H34O2
Molar mass	378.556 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C5C6CC4CC5(CC(C6)C4)c(cc1O3)cc(O)c1C2CC(C)=CCC2C3(C)C;
	InChI InChI=1S/C26H34O2/c1-15-4-5-21-20(6-15)24-22(27)10-19(11-23(24)28-25(21,2)3)26-12-16-7-17(13-26)9-18(8-16)14-26/h4,10-11,16-18,20-21,27H,5-9,12-14H2,1-3H3/t16?,17?,18?,20-,21-,26?/m1/s1 ; Key:RPBMPWGKZFLMFN-OKFSJJLXSA-N ;
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AM-411 (part of the AM cannabinoid series) is an analgesic drug that is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with an adamantyl group at the 3-position, demonstrating that the binding pocket for the alkyl chain at this position can accommodate significant bulk.

AM-411 is a potent and fairly selective CB₁ full agonist with a K_i of 6.80 nM, but is still also a moderately potent CB₂ agonist with a K_i of 52.0 nM.[1] It produces similar effects to other cannabinoid agonists such as analgesia, sedation, and anxiolysis.[2][3]

References

Lu, D.; Meng, Z.; Thakur, G. A.; Fan, P.; Steed, J.; Tartal, C. L.; Hurst, D. P.; Reggio, P. H.; Deschamps, J. R.; Parrish, D. A.; George, C.; Järbe, T. U.; Lamb, R. J.; Makriyannis, A. (2005). "Adamantyl cannabinoids: A novel class of cannabinergic ligands". Journal of Medicinal Chemistry. 48 (14): 4576–85. doi:10.1021/jm058175c. PMID 15999995.
Järbe, T. U.; Dipatrizio, N. V.; Lu, D.; Makriyannis, A. (2004). "(-)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: Effects on open-field behaviors and antagonism by SR-141716 in rats". Behavioural Pharmacology. 15 (7): 517–21. doi:10.1097/00008877-200411000-00008. PMID 15472574.
McLaughlin, P. J.; Lu, D.; Winston, K. M.; Thakur, G.; Swezey, L. A.; Makriyannis, A.; Salamone, J. D. (2005). "Behavioral effects of the novel cannabinoid full agonist AM 411". Pharmacology, Biochemistry, and Behavior. 81 (1): 78–88. doi:10.1016/j.pbb.2005.02.005. PMID 15894067.

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[1] Lu, D.; Meng, Z.; Thakur, G. A.; Fan, P.; Steed, J.; Tartal, C. L.; Hurst, D. P.; Reggio, P. H.; Deschamps, J. R.; Parrish, D. A.; George, C.; Järbe, T. U.; Lamb, R. J.; Makriyannis, A. (2005). "Adamantyl cannabinoids: A novel class of cannabinergic ligands". Journal of Medicinal Chemistry. 48 (14): 4576–85. doi:10.1021/jm058175c. PMID 15999995.

[2] Järbe, T. U.; Dipatrizio, N. V.; Lu, D.; Makriyannis, A. (2004). "(-)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: Effects on open-field behaviors and antagonism by SR-141716 in rats". Behavioural Pharmacology. 15 (7): 517–21. doi:10.1097/00008877-200411000-00008. PMID 15472574.

[3] McLaughlin, P. J.; Lu, D.; Winston, K. M.; Thakur, G.; Swezey, L. A.; Makriyannis, A.; Salamone, J. D. (2005). "Behavioral effects of the novel cannabinoid full agonist AM 411". Pharmacology, Biochemistry, and Behavior. 81 (1): 78–88. doi:10.1016/j.pbb.2005.02.005. PMID 15894067.

AM-411

See also

References